Aug. 27, 2025

Autonomy’s Moment Is Now. Austin Is the Autonomy Capital | Jeff Cavins, Outdoorsy Group

Show Notes

Autonomy’s moment is now as the operating stack goes live across software, hardware, availability, and insurance. Outdoorsy Group CEO Jeff Cavins joins the show to unpack how RoboTaxis integrate with marketplaces, city systems, and the consumer experience. Austin’s talent, technology, and risk appetite are making it the Autonomy Capital.

Highlights

01:31 Why Outdoorsy Group is betting on RoboTaxis
05:44 Software must command the car
10:40 RoboTaxi as the default transpiration benchmark
15:30 FSD & the Airport
25:39 Coverholder status and dynamic underwriting
32:26 Austin’s autonomy flywheel
41:50 Safety is the X-factor
45:52 Cargo, errands, agentic ops
51:29 Autonomy in air and ground
58:44 What’s Next Austin?

Guest Bios
Jeff Cavins is a distinguished technology veteran with over 22 years of senior-level experience leading and transforming emerging growth technology, software, Internet, and digital media companies. His illustrious career has been marked by significant value creation, contributing to over $32 billion in total market capitalizations. As the Co-Founder and CEO of Outdoorsy Group, he steers a global leader in mobility and accommodations, encompassing Outdoorsy, the largest and most trusted peer-to-peer RV rental platform, and its pioneering insurtech arm, Roamly.

Jeff's leadership at Outdoorsy Group is rooted in a deep understanding of market dynamics and a relentless pursuit of innovation. This is exemplified by Roamly's recent achievement of Lloyd's Coverholder status, a testament to its specialized underwriting expertise in complex, niche markets. This strategic move positions Roamly to enable the future of shared mobility across RVs, campervans, carsharing, and even emerging transportation like cybercabs.

Before co-founding Outdoorsy in 2015, Jeff served as Chief Executive Officer of Fuze, a cloud communications company recognized by Inc. 500 as the 125th fastest-growing private company in America in 2013. His tenure at Fuze included overseeing the development of "Fuze for iPad," a product personally used by Steve Jobs and featured in Apple's 2011 "We Will Always" global iPad TV ad campaign.

Prior to Fuze, Jeff was President and CEO of CallWave (NASDAQ: CALL), a leading provider of internet and mobile-based unified communications solutions. He also served as CEO of Loudeye Corporation (NASDAQ: LOUD), a global leader in digital media distribution technology, which was subsequently acquired by Nokia. At Loudeye, he masterminded the company's global expansion and forged strategic partnerships with industry giants such as Apple, AT&T Wireless, Nokia, and Virgin, ultimately growing shareholder value by over 1700 percent.

Jeff's extensive experience also includes serving as a Venture Advisor at Azure Capital Partners in San Francisco, and as Senior Vice President for Exodus Communications, where he managed over $1.3 billion in revenue and 1,900 employees. There, he established crucial strategic partnerships with industry leaders like Google, Yahoo!, eBay, and MSN.

Earlier in his career, Jeff founded, presided over, and led CSI Digital, an advanced digital media technology software company specializing in visual effects for the TV and film industries. CSI Digital earned recognition from Inc. Magazine in 2007 as the 100th fastest-growing private company in America and was awarded first place in the inaugural Deloitte and Touche Fast-50 Program in the same year. He began his career with nearly a decade in the broadcast division of Sony Corporation, where he held sales management and engineering roles, and notably designed and developed the Instant Replay system for the NFL, leading its deployment across the league.

Guest Links
Jeff Cavins: LinkedIn
Outdoorsy Group: Website, LinkedIn, Instagram
Roamly: Website, LinkedIn, Instagram